I've been in Hell long enough to know there is no such thing as redemption. There is only promises and bargains and tricks we play on ourselves to make us believe we're good people... I'm not a good person. I own that. And if I'm going down... I'm going out with a bang.

Malachai "Kai" Parker is a major recurring character and the main antagonist of the sixth season of The Vampire Diaries. He also appears as a recurring character in the eighth season of the series. Kai is the son of Joshua Parker and his unnamed wife, as well as the twin brother of Josette, and the the older brother of Olivia, Lucas, Joey, and three other unnamed and deceased Parker siblings. However, when his true nature as a Siphoner was revealed in adolescence, his family began to treat him poorly and referred to him as an "abomination," which, among other factors, led to him growing up to be a sociopath.

He was first seen trapped in a prison world with Damon Salvatore and Bonnie Bennett. Kai unwillingly formed an alliance with Damon and Bonnie in hopes that they could all escape the parallel dimension and return to the real world.

Eventually, after Bonnie sacrificed her chance to escape in order to ensure Damon could return to the living world, Kai and Bonnie were the only two left in Kai's metaphysical prison. Later on, he and Bonnie attempt to escape the prison world, but Bonnie stored her magic in a teddy bear and sent it back to the real world as well so he couldn't force her to help him escape. Though he was enraged by this act, Kai brought Bonnie to his childhood home in Portland, Oregon and cooked her a Thanksgiving meal. However, he later betrayed Bonnie, taking the knife his sister's magic was stored in and stabbing Bonnie in the stomach with it to gain her Bennett blood to use to escape.

Kai eventually freed himself from the 1994 prison world, after which he made it a point to antagonize the Mystic Falls Gang, as he sought to kill his surviving siblings and merge with Jo, regardless of the consequences. However, in Prayer For the Dying, his younger brother Luke attempted to merge with him instead. Kai ultimately overpowered Luke and absorbed all his magic (as well as his ability to produce and retain his own magic) during the merge. Soon after, Luke's essence also merged with Kai, passing down his emotional capability and capacity for empathy, which mellowed Kai out, making him less evil and even allowing him to briefly work with the Mystic Falls Gang as an ally. However, in A Bird in a Gilded Cage, Bonnie, who was still holding an understandable grudge toward him for the torture he put her through, left him behind in the 1903 prison world with the Heretics, a group of former Siphoner exiles from the Gemini Coven, who had been turned into witch-vampire hybrids by Lillian Salvatore sometime in the 19th and 20th centuries.

In the Season Six finale, I'm Thinking Of You All The While, Kai escaped the 1903 Prison World with the Heretics, cloaking their location from Lily in exchange for her blood so that he could be turned into a hybrid as well. He killed Jo and, seemingly, her twins at her wedding to Alaric Saltzman to avoid any competition for the role of leader of the Gemini Coven. Kai then wiped out the coven through his suicide, killing his father and other coven members in the process and thereby rendering the Gemini extinct. Kai woke up and transitioned into a witch-vampire hybrid, but was decapitated by Damon Salvatore soon after out of revenge for placing Elena in a mystical slumber until Bonnie dies.

In What Are You?, Kai is temporarily able to return from Hell, with the ringing of the Maxwell bell. Kai attempted to enter a bargain with Cade in order to remain in the living world and successfully did so by giving him Elena's coffin. Later on, he attempted to kill the last remaining Gemini witches, his nieces: Lizzie and Josie Saltzman. After he failed, he was permanently banished and imprisoned in the newly created 2018 Prison World by Bonnie, Lizzie and Josie.

Kai is a member of the Parker Family, and is the last leader of the Gemini Coven.

Early History


Kai's family in the newspaper on May 10, 1994 after he massacred them

Malachai was born in Portland, Oregon in 1972 as the eldest son of Joshua Parker and twin brother of Jo. As a siphoner, he was shunned by his family, even revealing to Caroline that he wasn't allowed to touch anyone. As twins of the Gemini Coven, Kai and Jo were expected to merge. However, Joshua knew that Kai would win the merge given his powers, and knew that Kai could not lead the coven. Due to this, Joshua and his wife kept having children until another pair of twins was born: Liv and Luke.


Kai attempting to merge with Jo.

Realizing this, on May 9, 1994, he decided to kill his siblings and merge with Jo. He stabbed Jo with a hunting knife to get her out of the way as he went after their siblings, but Jo managed to cloak the twins to protect them, promising to merge with him so long as Liv and Luke could live. However, she had relinquished her magic, and the coven harnessed the power of a solar eclipse to trap him in a purgatory dimension for his crimes, which kept him trapped in a snapshot of the day that he was imprisoned.

In the Prison World, Kai tried to kill himself several times, each unsuccessful.

Throughout The Vampire Diaries Series


First meeting Kai

In Welcome to Paradise, Kai made his first appearance on the show at Bell's Market in the otherworldly-Mystic Falls, when Damon encountered him after having a fight with Bonnie. After a few comments here and there, Damon lost his patience and attacked Kai, who managed to calm him down and trick him into drinking some bourbon laced with vervain. The vervain weakened Damon to the point where he was not able to fight Kai off. The latter quickly made a stake out of broken patio furniture and stabbed him in the hand, with the intention to eventually kill him when Bonnie finally arrived. She demanded that Kai leave Damon alone, but Kai quickly brought up her inability to perform magic and mentioned that he had been watching them both for months, including their fights and her failure to regain her powers. He then was about to stake Damon when Bonnie, desperate to save him, managed to regain her magic by lighting a nearby candle. Realizing she could practice witchcraft again, she told Damon to run and then lit all of the spilled bourbon on fire, creating two walls of flames around Kai. Kai tried to calm Bonnie down, but Damon came up behind him and knocked him out with another piece of patio furniture. He was later seen at the Salvatore Boarding House, where he was tied to a chair by Damon and Bonnie so they could begin questioning him on why he tried to kill Damon. He finally revealed that he only did it to use fear to trigger Bonnie's magical abilities again, before admitting the most important detail—that Bonnie's magic is the key to their escape out of their dimension and back to the real world.

In Black Hole Sun, Kai - who is still tied up - asks Damon why he believes the Dimension is his own personal hell and what happened to make him think such a thing before Bonnie comes into the room and gives him a couple of supplies that he'd apparently asked for: can-opener, shower-drain, grinding wheel, jam, a pocket knife, volume O of the encyclopedia, a nail and a black marker. Damon asks him what that "pile of crap" is going to do to get them out and Kai says he'll explain as soon Damon tells him what happened in his life on May 10, 1994 as Bonnie's powerful magic is one part of the equation, Kai's general undisclosed knowledge the other and Damon's story is the last part, as it will supposedly help them figure out why they're stuck on the same day. Damon reveals that the worst thing he ever did was on that day and he wishes not to talk about it, which only inspires more sarcastic curiosity from Kai and Damon begins to tell his story.

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Kai falls asleep

Soon after, Kai falls asleep and when Damon comments on that, he claims he was awake the entire time and that Damon "totally" killed the pregnant woman much to Bonnie's surprise as Damon does not deny it. Damon then threatens Kai with death if he doesn't inform them of how they are going to get out. Kai then tells them that to get out, they'll need to channel/harness the power of the daily eclipse using a mystical relic called an Ascendant and that the last time anyone saw one was in the Pacific North-West Oregon and that it belonged to his family and all they need is a locator spell from Bonnie and he gives her his blood. When Bonnie prepares and fails her spell, Damon tells her she sucks at magic now. Kai tells her to ignore Damon, and that he used to tune out his many brothers and sisters by pretending they were white noise machines, but it taught him to focus. Kai begins to flirt with an amused Bonnie before Damon says, "Hey, there, "Big Brother", she doesn't know you, at least buy her a drink." Bonnie starts the spell again later and this time, it begins to work. The blood on the map shows them to Mystic Falls. Bonnie feels that it's very close to them and touches Kai on the chest, saying that it is on him and he pulls the Ascendant out of his pocket and says that Bonnie is "very good". Damon is not amused with Kai's mind-games as it was a simple waste of time, but Kai tells them that he was testing her power, to see if her magic was precise enough and that she's ready for the spell. Later, Kai is looking for the right spot to channel the power of the eclipse when Bonnie tells him he could've shown them the Ascendant to begin with and he says he wanted to feel her hand on his chest. Kai figures out where they need to be standing for the spell and Bonnie finds a newspaper that says a family was killed off and the only missing one was the oldest named "Malachai" and Kai overhears and says, "Who names a kid Malachai? Its like they expected me to be evil." He reveals that he killed off most his Coven/witch siblings, killing everyone but his sister, whom he only ripped out her spleen because he had "soft spot" for her. He shows his sociopathic side by saying that his last brother fought hard and he was like, "I saved you for last, you ungrateful, little . . ." He reveals that he is, in fact, a witch, but with no powers and that when the Gemini Coven found out what he'd done, they vanquished him to the dimension as his prison, not Damon's. This inspires Bonnie against Kai and she refuses to do the spell as the eclipse comes and she says that she won't bring a killer back into Earth no matter how badly she wants to live.

Kai informs them that it's a win-win, they do the spell, they can go back to their friends and he can painfully kill off the remnants of the Gemini Coven. Bonnie refuses even after being begged by Damon and Kai seemingly wants to inspire her with physical trauma and Damon vamps him to a wall before he can and tells him that regardless of their disagreement, he can never lay a hand on Bonnie, but Kai no longer cares as the day's eclipse is over and he calls a rain-check for tomorrow, but Bonnie continues to refuse and leaves.

Malachai using Bonnie's power

Kai using Bonnie's power

Later, when she's having dinner, Bonnie tells Damon that he isn't a monster because feels remorse for his actions, that's the difference between him and Kai, Kai feels joy, not remorse and that there's hope for Damon. Damon suggests that they can still get out, they can steal the Ascendant from Kai, find out what he knows and then ditch him, which would be easy given the fact that he doesn't have any powers. Kai, enters, having overheard their conversation and tells them that it isn't necessarily true and that he does have powers, but they have a "killer effect" on witchcraft: he can't generate it, but he can absorb it temporarily from others. He then clasps Bonnie's wrist and his hand glows red as he ingests Bonnie's extreme power, then he gives Damon an aneurysm and gives them an ultimatum: they'll do as he says and give him what he wants - a way out along with them, or he'll take Bonnie's powers completely, leaving her dead and then kill Damon and do the spell himself.

In The World Has Turned and Left Me Here, Kai meets up with Damon and Bonnie in the woods in preparation for the ritual. He tells them that the eclipse will happen directly overhead in perfect alignment with the Gemini constellation. He also informs them that they need to do the spell underground and let the light of the moon and the sun pour through a hole that Damon’s meant to dig up and that when the light comes down, it will activate the power of the Ascendant and anyone touching the relic in the sun will be able to portal-jump back to Earth. Bonnie asks him if she can see the spell and Kai informs her that he will before saying he’s going to town to get some supplies. Kai returns to find that Damon’s done digging and a suspicious Damon looks through his backpack and sees supplies from back in the day – Zima, grunge, most Alex Rodriguez rookie cards on demand and a pager, which Damon ridicules. Kai defends himself by saying he’s super-excited by the future and the Internet and all, but 1994’s always been his home and he doesn’t want to give up his “digits” – 555-Hiya-Kai, there’s no way he’s giving up those digits and since these things are old and from back in the day, once he’s in the 21st century, he wouldn’t want to get homesick. Bonnie says that she isn’t going into the caves until Kai shows her the spell. Kai simply stands smiling and refusing to show it to them until they’re in the caves. Bonnie says fine, since he knows the spell and doesn’t want to show it to her, he can do it himself and since he wants her magic, she outstretches her hand and tells him to take it. She says she’s serious since it was his big threat that he’ll take her powers and kill them both and do the spell by taking all her power. “Don’t mind if I do” Kai says and begins to kill her while absorbing her powers. Damon is worried, but Bonnie – still being drained – tells him not to act and that Kai won’t kill her. Kai goes on for a period of time, suggesting that he’s serious until he let’s go and Bonnie’s correct. Bonnie realizes that he doesn’t know the spell, which means they don’t need him. Then she says “Motus!” and telekinetically stabs him in the chest with an axe, which kills Kai immediately, much to Damon’s disappointment as he knew more than even Bonnie does.

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Kai - after being stabbed by Bonnie - dies

Bonnie soon figures out that the dimension was created by a spell that was created by a Bennett Witch, as such, only a Bennett can do the spell to get them out and Kai truly was lying (which is why Grams put them there) and that’s why he wouldn’t kill her and she uses her powers to activate the first part of the Ascendant. Before the sun-moonlight can work when Bonnie and Damon are together underground, Kai shows up and shoots Bonnie in the abdomen with a crossbow. Kai tells them that he’s tried to kill himself many times and that he can’t die as part of his punishment in the Other Dimension. Damon and Kai struggle as Bonnie wounded is weakened on the ground. She grabs the Ascendant and says she’s not going to make it as the boys continue to struggle and she smiles and informs Damon that he’ll make it and uses the Motion Spell to levitate Kai into the wall and pushes Damon telekinetically into the light of the eclipse and throws the Ascendant into his hands, using her powers to send back to Earth as a now hopeless Kai screams in rage, left in the chasm with a weakened and saddened Bonnie.

In Do You Remember the First Time?, Kai has taken Bonnie to the boarding house, has taken care of her wound and is still struggling with fixing the Ascendant while also waiting for Bonnie to wake up. After she finally does, he wonders if she's okay, much to her dismay as she immediately tells him that she won't help him or release him. He responds to this by grabbing her hand and showing her that she has no power over him as he can drain her magic with a touch. She, however, grabs a pen and quickly stabs him in the neck, temporarily killing him. She then proceeds to collect all of the Ascendant's pieces and runs away. Later on, Kai finds Bonnie in the hospital just when she manages to fix the Ascendant only to realize she's missing one piece - the one Kai has. He claims he found her by the trail of blood, though she quickly attacks him by sending all of the objects in the room onto him, as well as attacking him with electricity which slows him down. As she gets back to Damon's car, Kai shows up and grabs her from behind. He then claims that Bonnie will do the spell again to get them both back home. They're later seen down in the cave again where Kai gives Bonnie her teddy bear from her childhood, claiming it's his gift to her. He then claims he wants to be better and rejoin his family by saying that the 20 years he's spent in this prison have made him realize his mistakes. Bonnie brushes it all off and starts doing the spell. She stops in the middle, claiming she's lost her magic. Kai grabs her to see if she's lying only to figure out her power is gone. She then reveals she stashed it away somewhere safe. As soon as Kai realizes where she hid it, it's too late since the teddy bear in which Bonnie put her magic is already gone, sent back to the mortal plane for Damon to find. He gets angry and approaches Bonnie violently as he realizes that her magic is gone, to which she responds by saying that they're stuck there forever.


Kai cooking dinner for Bonnie

In Fade Into You, Kai is seen taking a bound Bonnie out of a car trunk. It is revealed he took her back to his family's house, where he grew up. Kai then makes Bonnie a Thanksgiving dinner. She dislikes eating with Kai and wants to leave. Kai eats slowly, but agrees to allow Bonnie take the car when he's done. While eating, he explains his dark history to Bonnie, to which she is not amused. Later on, Kai discovers that his sister, Jo left her magic-imbued knife in a tree stump and Kai grabs it. He stabs Bonnie without hesitation and it is implied he returns to the living world.

In I Alone, Kai is riding in a taxi and is talking the driver's ear off. He mentions the technological advances present and also complains about skinny jeans. Eventually, he reaches his destination, where Liv is. Since he had no money, he kills the taxi driver with a pair of headphones and exits. Kai asks Liv for a drink, but she believes he's too young. When he shows her his ID, she still refuses him a drink. He then reveals that he is the brother that tried to kill her and Luke. Liv backs away, but Kai takes some of her magic. As Liv attempts to escape, she runs upstairs and Kai follows. Before he can kill her, Tyler pushes him over the railing and Kai flees. Eventually Kai reunites with Damon and meets Elena. He weakens Damon and sets Elena on fire. However, Damon attacks him and knocks Kai into Mystic Falls. He then teases them, saying that there's a psycho loose in Mystic Falls and no vampires can stop him, because of the anti-magic border. Kai is later seen paying Tyler a visit, offering to save Liv's life if the two can arrange a deal.

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Kai, Luke, Liv and Jo reunited in the crypt

In Christmas Through Your Eyes, Kai attacks an innocent woman who lands up in the hospital, knowing that she will be helped by Jo. When the time comes for Jo to operate on the woman, Kai kills the doctors who're in the room with her as she asks what happened to the girl and he grabs her from behind, whispering in her ear "I stabbed her." and then injects Jo with tranquilizer. Later, Kai is seen at the cemetery with Liv and Luke. It is revealed that, in order to escape the Merge, Liv and Luke located Jo's Knife (on this plane) and Kai wants to "reunite" Jo with her powers through it. He has chained her up in a crypt. Jo demands what he did to her and he says that he hasn't seen her in eighteen years and she can't muster a hello. He stabs her in the shoulder, claiming to be trying to give her back her magic. Luke intervenes, trying to stop him after he stabs her again. Kai then shoves Luke into a wall and reminds him that he wanted to kill him when his brain was the size of an acorn and he doesn't have a problem doing it now. Luke shoves Kai away from him and walks out, saying he will not watch the current events unfold. Kai laughs after he leaves, shoving more signs of sociopathy in his eyes calling Luke "dramatic", much to Liv's visible annoyance. He then kneels and looks at his sister, telling her that they can try this again, but Jo tells him that she put her magic into the knife by choice, taking it back is also her choice, unless she bleeds to death which is in the next thirty minutes and she laughs, smugly informing him that it would be ironic if he accidentally killed her before the Merge ceremony. Kai gives Liv the knife and tells her that she had better find a way to put their sister's magic within the dagger or he will use it to slit her throat and then leaves to get a bandage. Kai returns, overhearing Liv pep-talking Jo, informing her that she has come a long way without magic and she could become more with it. Kai then grabs Liv's shoulders, absorbing her magic and knocking her to the ground as it brings her pain. Kai then begins to give her an aneurysm and asks Jo if it will be funny when he kills Liv with her own magic and verbally ponders whether that would be funny or sad as he apparently gets his emotions mixed up. As he goes on hurting Liv, he asks Jo what is the spell for fire again and he correctly guesses it is incendia. But before he can use the spell, Jo cries enough and grabs the dagger, absorbing the power inside as the candles all around the crypt set alight and the winds blow. Jo pants as she feels the rush of power again and Kai kneels and his hands hover over Jo's face and he senses her power. He then tells her she is predictable as he threatened Liv in order for her to feel the need to save her using magic. Jo destroys the chains that hold her with a spell, but before she can attack Kai, he hears something from outside and goes to check it out. It is Damon whistling and he attacks Kai, throwing him to a tree, dazing him for a moment. Kai gets up as Damon taunts him and uses a Motion Spell against Damon, throwing him through the threshold of the anti-magic boarder. Damon begins to die and runs out quickly as Kai walks into it, ensuring his safety. Kai, thinking he is safe, is sneak attacked by Alaric from behind, who holds a pistol to his head. Damon thanks Alaric and tells him to kill Kai before Jo arrives and tells them that he can't kill Kai as she does not think that it is fair to Luke and Liv to be forced to do the Merge. She also says that she can win against Kai in the Merge as she has regained her magic, she just needs to get stronger. She implores Alaric not to and as Kai smiles at the scene, Alaric instead hits him over the head with the pistol instead of killing him, much to Damon's annoyance.


Kai threatened by Damon and Alaric

When Kai awakens, he has been chained by Alaric to a tombstone. Damon - from beyond the border - throws stones at Kai, failing attempts to kill him. Kai talks as Damon continues, asking Damon how the anti-magic border works, "Is it like a dome or a bubble?". Damon throws another stone that only hits a tombstone as Kai goes on, "Like, say you were in a 747 flying over Mystic Falls, would you die?". Another stone misses but Kai continues, "You know, that could be dangerous, like if you're headed to New York and your pilot reroutes for weather." Damon suggests that once he's dead and in Hell, he can ask a bar full of dead Travelers who cast the spell. Kai thinks aloud that that is a lot of Travelers and must've been a pretty give spell, which gives Kai an idea and he quietly says that it is so big that it covers every inch of the entire town. Kai then touches the earth with his hand and closes his eyes in concentration.  While Damon and Alaric argue, Kai lightly touches the ground and the earth glows red where he touches it, indicating that there is magic there and Kai feels the magic and grins. While Damon and Alaric continue to mind their own business, Kai decides he will absorb the power and begins to chant a spell. Damon and Elena are on the phone and while they talk, the winds pick up and the powerful magic Kai is doing begins to mess with the very technology of the reception. Kai deepens his fingers into the earth and the red glow intensifies and this power melts the chains that hold him while he simultaneously continues to take in the Traveler Magic. Damon suddenly notices that Kai has stopped talking as he never stops talking while Kai begins chanting a spell as the incredible power begins to turn him into a witch. He fully absorbs the power, deteriorating the power of the anti-magic boarder and he stands. Kai stands up, fully powered and confronts Damon and Alaric. Damon voices that he's guessed what Malachai has done, "You little magic-sucker. Sucked up all that magic from the Traveler Spell." Kai tests out how powerful he is, making the winds blow hard and levitating Alaric over ten feet in the air and onto a tree and Kai says "A lot of magic."


Kai knocking Elena out.

Kai is attacked by Damon, who holds him to a tree. Kai easily pushes the vampire back, who then attempts to punch Kai before he simply turns invisible. Later, when Elena is outside the Salvatore Mansion, Kai cloaks her and himself and Damon does not hear or see her as she talks to him, revealing that he has used a clocking spell on them. He then knocks Elena out and abducts her for an unknown reason.

In Woke Up With a Monster, Kai is first seen through Elena's eyes when she wakes up on a table in the grill. She asks why is she here, he responds with your here to help me to control my magic. He then uncovers the manager of the grill's dead body from his cloaking spell. Kai claims that he was just trying to put a cloaking spell on him when his powers decided to do otherwise and ended up killing him and eventually successfully succeeded with a cloaking spell. Kai then moves Elena to the high school when he ties her up to the lights in the ceiling. Kai attempts different spells on Elena including writing the first letter of his make on Elena's forehead and causing her blood to boil causing her daylight ring to melt. Elena then escapes and sets her hand on fire and puts it in front of the gas and blew Kai away. Kai later, catches up with Elena and attempts to snap her neck with magic but takes three times until he successfully snapped her neck. Kai then resumes practicing his magic on Elena. He is next seen walking past Jo and Damon (who were cloaked) and putting something in the bin. After Jo had cloaked another person it became difficult for her to maintain and resulted in Kai seeing them. Kai then experiments with his newly controlled powers creating an illusion that he was Elena. Damon throws a stake at "Kai" and who is really Elena. Kai says he's getting good. But gets knocked out by Damon.

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Luke convincing Kai to merge with him

In Prayer For the Dying, Damon wakes Kai up from his induced coma because he wanted Kai to siphon the magic out of Liz. Kai does this but disappears after Jo sees him. Later, Kai and Jo start to Merge, however, Luke intervenes knocking Jo out with magic and offers to merge with Kai instead. Due to the fact that his imprisonment had kept Kai at the age of 22 so they were basically the same age and that they were of the same bloodline, it provided the needed loophole to allow them to attempt the Merge. Luke dies during the Merge and Kai now has permanent magic.

In The Day I Tried To Live, Kai is first seen at the Salvatore Boarding House, interrupting Elena and Damon, asking them if they'd seen Jo. He then explains that after the Merge, once he had killed Luke and gained his powers, he also gained some of Luke's humanity. he claims that he feels bad for what he has done to Luke. He states that he started writing a letter to Jo and found himself crying. Later, Elena and Damon ask Kai if he can fix the ascendant from when he broke it the last time. Kai responds that it can't be repaired but part of it can be used to return as a ghost. Kai later performs a spell and Jeremy, Elena, Damon and himself find themselves in the prison world overlooking Bonnie. However, Bonnie cannot see or hear them as they are just projections. Not long after the spell is cast, they find themselves back in the present and Kai's nose is found bleeding from the drain of magic. The magic that it costs to hold four people in the prison world is too great. He then suggests that he should only take one person. Kai finds himself bleeding through his stomach and finds themselves back in the present with Liv holding a poker through Kai. Liv tries to immobilize him but Kai uses magic to throw a fork into her neck. He then downs alcohol all over her and holds a candle above her but for some reason, can't seem to drop it. Liv takes advantage of the situation and flings a fork at Kai again, Jeremy then wakes up and flings a knife at Liv and drags Kai into the kitchen and begs him to send him back. Kai starts chanting and they both find themselves back in the 1994 prison world. Once Jeremy had saved Bonnie, Damon fed Kai some of his blood, healing him of his injuries.


Kai seeking help from Jo

In Let Her Go, Kai turns up at Jo's door claiming that he wasn't feeling so good and was coughing up blood. Jo checks him out and responds that everything appears to me normal, then coming to a conclusion that it is something magical making him that way. It is revealed that is Kai dies, the entire Gemini Coven dies with him, also Prison Worlds would collapse. Killing anyone inside of them. Kai starts to cough up more blood and grabs Jo's wrist, accidentally absorbing some of her magic making Jo squirm with pain. Alaric quickly intervenes and disconnects Kai from Jo. Kai claims that made him feel a lot better and that Jo needed to give her magic to him. Jo claims that it will kill her. Kai just tells her to put it in a teddy bear or a knife like she did last time. Alaric says that she doesn't have to. Later, once Jo had made up her mind, she decided to give up her magic again. She placed her hands on Kai's head and started chanting, storing her magic in Kai making him all the stronger. Kai then whispers in Jo's ear that she was pregnant and walked out.

In The Downward Spiral, Kai is first seen, in the Salvatore Cemetery, talking to Damon about the fact that his mother must have been a vampire, otherwise how could she be alive, as Damon breaks open his mothers coffin as he is convinced that she is inside it and not in the 1903 prison world. Next, he is seen in the Salvatore Boarding House, breaking things as Damon is on the phone to Stefan. Then Damon asks Kai is it is possible to send him back to the 1093 prison world. Which he responds with yes. However, he needs the ascendant for the 1903 prison world which he doesn't possess at the moment but apparently, it won't be hard to find and he will only get it if he can talk to Bonnie. Later, Kai walks in after Damon finishes his failed attempt on Bonnie on the phone to try and get her to agree to meet up with Kai. He replies with "that's a shame" implying that he knows something and states that he has a strong lead on the ascendant and that Lily was ambushed on a dock in New York City in 1903. Damon and Kai turn up at the rave looking for Bonnie and ignoring what she said about never wanting to see Kai ever again. Once Kai sees Bonnie, he attempts to speak to her, but she does not listen and storms out of the rave in anger. Kai is then seen walking back into the Boarding House, Damon forces Kai to tell him why his mother was stuck in the 1903 prison world and says she was imprisoned because she has killed over 3,000 people and like Stefan, she was a ripper.


Kai watching Bonnie do her spell.

In A Bird in a Gilded Cage, Kai helps Damon to get his mother back so she can help him get Stefan's humanity, so he sends Bonnie, Damon, Elena and himself the 1903 prison world where Elena and Damon go and find Lily, Kai and Bonnie look for the ascendant. While Bonnie is performing a locator spell, Kai continues his apology but ends up grabbing Bonnie by the wrists because she wasn't listening to him. They both head towards the ascendant, but Bonnie wants to get her revenge on him for letting her alone in 1994 so she stabs him in the back and then leaves him in the prison world where he would be alone like she was. Later, Kai stumbles upon a dark cave which he later discovers is inhabited by 6 desiccated vampires from Lily's den. Kai gets too close to one of the vampires and ends up getting used like a blood bag.

In I Could Never Love Like That, Kai is only mentioned by Elena, but it is revealed that the vampires in the 1903 prison world are no ordinary vampires, they, like Kai, could siphon magic. Even though they had been turned into vampires they retained their ability.

In I'd Leave My Happy Home For You, Kai is seen briefly making dinner for the Heretics. It appears they have also have been feeding on him as well. As he rings a bell to reunite the vampires for dinner, he mentions that today is a big day, that it was time to get out of the prison world.

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Kai ruining Jo and Alaric's wedding

In I'll Wed You in the Golden Summertime, Kai is first seen in Bonnie's dream. While she was running away from Lily, Bonnie crashes into Kai. She tries to cast a spell on him but realizes she no longer has her magic. Kai says that it might be his fault since he was spooning her earlier and might have sleep siphoned her. He then indirectly tells her that she can't keep screwing people over or else there will be consequences. Towards the end of the episode, Jo is stabbed multiple times in the lower back. As she collapses into Alaric's arms, Kai turns off his invisibility spell and appears behind his sister, bloody knife in hand. He then inflicts a massive aneurysm to all the attendants of the wedding and destroys most of the church's windows and fixtures by producing high-frequency sound waves.

In I'm Thinking Of You All The While, Kai is first seen at the church when he snaps both Stefan and Caroline's neck, claiming that it was now family matter now. He gives Alaric his meaningless apologies for killing his bride and the twins, claiming that he didn't want competition for the leadership. The Gemini Coven, along with his father, tries to send him back to a Prison World, but they do, Kai stabs his neck with a piece of glass. He dies, killing all of the members of the Coven with him. Afterwards, he wakes up in transition and magically brings his father to him, licking his blood. He follows Alaric to his car, where Alaric shoots Kai, but it doesn't work since Kai is now a Hybrid. Before Kai can do anything else, Tyler, a newly turned werewolf, jumps on him and bites his neck, thereby infecting him with werewolf venom. At the Salvatore boarding house, Bonnie is seen with Matt, watching a recorded message from Kai. Kai explains that he put a sleeping spell on Elena so that she is linked to Bonnie. So only when Bonnie dies, Elena can wake up. He ends the message for Bonnie by telling her that it is all payback for what she did. In parallel, Kai arrives at the hospital where Elena's sleeping and ask Damon for help. Damon refuses to help him and demands that he explains what he did to his girlfriend. After Kai explains his plan, he leaves, returning to the church. While he's looking for blood, Bonnie arrives. She tells Kai to undo the spell he cast on Elena and her, while breaking some of his bones.
Kai 2

Kai's werewolf bite

Kai refuses and heals his werewolf bite by siphoning all of its magic. He then telekinetically throws Bonnie against a wall, nearly killing her. As Damon arrives at the scene, Kai gives him the option of saving Bonnie's life or waking Elena up by letting Bonnie die. Damon decides to leave, leaving Kai perplexed. He tells Bonnie that he wanted to see Damon suffer, choosing between his girlfriend or one of his best friends. But while he is distracted by wondering why, Damon comes behind him and decapitates him.

In Best Served Cold, Kai appears in Alaric and Jo's wedding tape.

In What Are You?, Kai surprised Damon and Alaric by showing up while they were trying to think of a way to kill Cade, and told them that he had a better idea than the one they had thought of.

In The Lies Will Catch Up To You,

"I would write... Dear Diary"

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In It's Been a Hell of a Ride, Kai attempted to enter a bargain with Cade in order to remain in the living world and successfully did so by giving him Elena's coffin. Later on, he attempted to kill the last remaining Gemini witches, his nieces: Lizzie and Josie Saltzman. After he failed, he was permanently banished and imprisoned in the newly created 2018 Prison World by Bonnie, Lizzie and Josie.


Kai was a charmingly unstable newcomer with the unsettling ability to seem normal as the situation demands. He can be both playful and obsessive with a mix of adolescent angst, likely stemming from the fact that he was referred to as an "abomination" due to his unique magical ability. He was shown to be a psychopath originally, after merging with Luke and gaining emotions, something he himself later confessed to. This was demonstrated when he killed four of his siblings with no remorse, for no apparent reason. He also called his brother ungrateful for fighting back during his murder. Furthermore, while killing his little sister with her own magic, he commented that the irony is funny, or sad, and that he gets those emotions confused, further demonstrating his lack of ability to feel remorse. He had also stated to be perfectly happy with who he was, even finding the idea of someone changing him funny.

He appears to enjoy killing people, as he has done so when other methods could easily have been used to escape the situation. He had also used the threat of murder to manipulate people into doing what he wants.

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Kai helps to bring Bonnie back

After the merge with Luke, Kai had absorbed some of his personality and had changed. He was far less evil then he as before and even shows signs of genuine emotion, such as feeling bad/guilty for killing Luke and his other siblings. He also showed selflessness, which could be clearly seen in The Day I Tried To Live, when he was "half-dead" and yet agreed to help Jeremy to go back in the Prison World after being heavily injured from their encounter with Liv, knowing that his magic could overwhelm him and kill him in the process.

In A Bird in a Gilded Cage, when Bonnie Bennett tried to kill him, despite the fact he changed and gained some empathy towards others, he didn't try to defend himself; he simply teleported away.

Despite the fact that he was no longer the evil psychopath he once was, Bonnie, nor his coven forgave him for his actions as they believed magic couldn't completely alter another's personality. Knowing this and feeling rejected, as well as finding out that the Ascendant was destroyed (to try and prevent him from escaping) and that Jo's children (twins) could take away his leadership of the coven, he became enraged and his old personality quickly resurfaced; as in his own words, he believed that if everyone thought he was incapable of redemption, he may as well prove them right. Kai, who was already unstable to begin with, became emotionally unbalanced, cruel, sadistic, ruthless and vengeful In I'll Wed You in the Golden Summertime, he stabbed his twin sister, Josette at her wedding multiple times in the lower back, killing his sister and (apparently) the twins, because he did not want any competition in the future. In I'm Thinking Of You All The While, after he was given Lily's blood (off-screen) he killed himself to wipe out his entire coven, as revenge for trying to permanently trap him in Lillian Salvatore's Prison World. Also, instead of killing Bonnie when he had the chance, he linked Elena's slumber with Bonnie's life, until the day the latter dies, as he believed she 'betrayed' him for being left in the prison world and told her it was "all your fault".

After becoming a non-original witch-vampire hybrid, Kai's emotions were heightened, including his negative traits; he became more cruel, sadistic, ruthless and vengeful, he also had a sadistic sense of humor, as he found Bonnie's emotional pain very amusing.

Powers and Abilities

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As revealed in Black Hole Sun, Kai had demonstrated that he possessed the ability to absorb a witch's power and use it as his own. This can kill said witch if Kai were to drain all of the witch's power for his needs. Aside from this ability, Kai has no other magical powers of his own, and can only practice magic by stealing the magical power of others. In Christmas Through Your Eyes, Kai absorbed the power of the Traveler's anti-magic spell on Mystic Falls, showing he can absorb power from active spells as well. 

Despite having no magical power of his own, he does have the tendency to simply appear out of nowhere when he's being talked about. An example would be when Damon suggested to Bonnie to steal the Ascendant and leave without him, and Kai just appearing in the hallway. Another example would be in Do You Remember the First Time?, when Bonnie attacks him with magic, and runs out to Damon's car, only for Kai to appear in the backseat.

He also demonstrated his coven's ability to turn invisible during his confrontation with Damon and Elena but only when he absorbed another witch's power.

Despite having no magical power of his own, he appears to have paid attention during his coven's teachings, as he was quickly able to use his powers to cast spells, showing that he has the knowledge required.
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In addition to having the ability to siphon magic, Kai can sense magic in others, but this power was limited to being close enough to touch the person he intends on sensing the power on.

However, the little time he had spent practicing magic has caused him to not be able to focus his abilities very well. It took him a few tries before he could get spells to do what they were supposed to do, however, after that he is capable of easily using them.

After Kai merged with his younger brother Luke his powers grew stronger, which gave him access to Luke's magic permanently. With his new-found powers after "The Merge", he considers himself mega powerful as the new leader of the Gemini Coven. Kai's recent spell was powerful enough to transport himself, Elena, Damon, and Jeremy to the Prison World in which Bonnie Bennett was trapped inside. However, they could not interact with Bonnie physically, and could only see her. After focusing all his magic to Jeremy, he was powerful enough to give him the ability to interact physically in the Prison World, saving Bonnie's life in the process and showing her where to get enough magic to get herself out.

As of Let Her Go, Kai's twin sister, Josette, transferred all of her magic to him making him even more powerful.


Kai casting a spell

Despite the fact that he now possessed the power of two witches, as he was only strong enough to take two people with him to the prison world and back to the real world, however, he later overcame this limit, as he had become strong enough to take all members of The Heretics (Valerie, Malcolm, Nora, Mary Louise, Beau and Oscar) back to the real world with him, (off-screen).

He had become so powerful, he was able to escape Lillian Salvatore's Prison World only with the blood of a Bennett witch without the Ascendant, combined with a the power of a recurring celestial event such as an eclipse or an Aurora Borealis, (off-screen) something that even Bonnie was unable to do, Kai was able to cloak himself and Lillian from Matt Donovan and Bonnie Bennett, despite the latter being a very powerful witch in her own right, as Bonnie was not able to sense his presence, even Damon Salvatore, a 174 year old vampire, with heightened senses was not able to sense Kai's presence, until the latter turned off his invisibility spell.

In I'll Wed You in the Golden Summertime, Kai was shown to be more powerful than all of the members of his coven, including his father, the former leader of the Gemini Coven, as he inflicts every individual attending Alaric and Jo's wedding with massive aneurysms, and he destroys most of the church's windows and fixtures by producing high-frequency sound waves, with a simple hand gesture; while he had a knife in his left hand.

He also cast a spell to link Bonnie to Elena Gilbert, causing the latter to be in a mystical slumber and stop aging as long as Bonnie is alive, Kai placed a fail-safe on this spell; if Bonnie or any witch tries to deactivate the spell, not only will Bonnie die, but Elena will die along with her, making sure there were no loopholes in this spell.

Kai possessed all the standard powers and abilities of a non-original witch-vampire hybrid.


Kai had the typical weaknesses of a siphoner.

Kai had the typical weaknesses of a witch.

Kai had the typical weaknesses of a non-original witch-vampire hybrid.


Jo Parker

Main article: Jo and Kai
Jo and Kai Christmas

Jo and Kai grew up together as witches part of the Gemini Coven. However, Kai was deemed as somewhat of an outsider due to his species-identity of being a siphoner instead of a regular witch. Their relationship is severely strained and antagonistic due to Kai wanting to be the leader of the Gemini Coven and killing most of their siblings, with the exception of their younger twin siblings (Luke and Liv). In the end, Kai killed Jo on her own wedding day and he died on the same day as well. Kai's death ended most of the Gemini Coven. Jo hated Kai for all of the atrocities he committed against her family and her, but Kai claimed to have loved Jo in his own way despite having the personality of a psychopath.

Bonnie Bennett

Main article: Bonnie and Kai

They first met in Season Five, after Kai attempted to kill Damon in order to reawaken Bonnie's magic. After spending time with Bonnie in his Prison World (along with Damon), Kai shaped up to be one of Bonnie’s dangerous enemies. Ever since they met and interacted in the 1994 Prison World, Bonnie loathes Kai for being a murderer. After the several murders Kai committed against other innocents (including his own family), Bonnie imprisons him in another Prison World. Bonnie did this to punish Kai for all his crimes against those she cared about and for those who were innocently killed because of Kai. Before Kai’s death, he escaped with the Heretics and became one of them. Kai later spelled and linked Bonnie’s life to Elena Gilbert’s. As revenge against Bonnie, Elena was forced into a magical slumber until Bonnie died a natural death in order to awaken again. In Season Eight, Kai returns from hell and decided to turn Bonnie and her friends’ lives upside down once again, which included him stealing Elena’s coffin. After the events of the eighth season, Bonnie imprisons Kai in yet another Prison World in 2018 and Kai is forced to listen to his most hated song for all eternity while chained to a chair in a restaurant. In the end, Bonnie got her revenge against Kai and all his wrongdoings.

Other Relationships


Season Six

Season Seven

Season Eight


  • The name Malachai is of Hebrew origin. It is a variation of the name Malachi, meaning "angel, messenger of God".
  • Other spellings of the name Malachai include Malachi, Malachie, Malachy, Malaki, Malakia, Malaquias, Malechy, Maleki, Malequi, Malakai, Malak.
  • Parker is an English family name, derived from the Old French with the meaning "keeper of the park".


  • According to Julie Plec and Caroline Dries, he could be irredeemable.
  • Since Kai was 22 years old at the time of his imprisonment in the year 1994, he would be 40 years old in current time, which is 2013 in the show's timeline. This means that Kai would be the same age or in the same age group as most of the main characters, such as Elena, Bonnie, Caroline's etc, parents.
  • Due to the nature of his prison, he is biologically 22, but chronologically 40.
  • Kai knows about vervain, however, as revealed by him in Welcome to Paradise, Kai does not have a lot of experience with vampires. In I'm Thinking Of You All The While, he reveals he did not even know werewolves existed until he was bitten by Tyler after he re-triggered his curse.
  • He can absorb power from other witches, even to the point of killing them, if he so chooses.
    • Kai is the first witch in The Vampire Diaries/The Originals franchise with this kind of ability.
  • Kai is one of only ten recurring characters that appeared in more than 10 episodes in their inaugural season. The other eight are Anna, who appeared in 11 episodes during Season One; Elijah Mikaelson, who appeared in 12 episodes during Season Two; Rebekah Mikaelson, who appeared in 17 episodes during Season Three; Atticus Shane who appeared in 11 episodes during Season Four; Nadia Petrova, Wes Maxfield and Enzo who appeared in 12 episodes each in Season Five; Jo who appeared in 17 episodes in Season Six and Rayna Cruz who appeared in 13 episodes in Season Seven.
  • He was a member of a coven, despite his lack of magical powers, until he killed the majority of his family. As punishment, the Gemini Coven trapped him in a purgatory dimension which Kai has referred to as his own personal hell. This revelation means that Damon and Bonnie are not actually in Damon's personal hell, which they originally thought upon their arrival.
  • There are similarities between Kai and Klaus' characters:
    • They are both different from the rest of their siblings, Klaus was born werewolf then turned hybrid, Kai was born as a warlock without magic but has the ability to absorb magic, and later turned into a vampire/witch hybrid who can siphon their own vampirism to maintain constant magical powers.
    • They both have hurt most of their siblings. Although in Kai's case, he killed most of them while Klaus prefers to neutralize his.
    • They are both called with abridged versions of their full names (Malachai and Niklaus) by most people.
    • They both needed blood from girls with supernatural heritage to free themselves from magical restrictions placed on them by their family
      • Klaus - Elena's doppelgänger blood to break the hybrid cure cast on him by his mother.
      • Kai - Bonnie's Bennett blood to free himself from his Prison World that his family sent him into.
    • Their fathers feel ashamed of them and abused and rejected them as a result. This causes them to be the way they are.
    • They both become the main figure in supernatural bloodlines, and their death would kill every member of those bloodlines.
  • He has voiced his disdain for his full name, stating it was like his parents expected him to be evil. Ironically, Malachai means "Messenger Of God".
  • Kai has tried to kill himself several times since being placed in his purgatory. However, as seen in The World Has Turned and Left Me Here, Kai comes back to life every time.
  • In Fade Into You, it's revealed that he can fly a plane as he flew him and Bonnie to Portland, it's unclear if he already knew how to fly or learned to during the last 18 years in the Otherworldly Time Dimension.
  • It is implied by Julie Plec and Chris Wood himself that Kai might have a crush or a thing for Bonnie.
  • In Christmas Through Your Eyes, Kai becomes supercharged with magic after absorbing the power from the spell of Traveler magic that created the anti-magic field around the Mystic Falls.
    • He also takes Elena Gilbert prisoner at the end of the episode, having knocked her out with a tire iron.
  • He shared his father's knack for cloaking spells.
  • Kai took Elena as a prisoner to practice using magic on her in Woke Up With a Monster.
  • Kai is the first one to know about Jo being pregnant as he himself told her the news.
  • Kai's powers are reminiscent of a warlock's from Charmed. Being able to absorb magical powers through killing the person possessing them.
  • In Prayer For the Dying, Kai siphons the magic of vampire blood in Liz's system to save her from dying from the effects vampire blood has on cancer.
    • This implies that he can kill vampires by absorbing the magic of vampirism which keeps them alive or undead.
    • This also makes him the only remaining thing that could kill an immortal besides Elena and Stefan's blood in conjunction with the traveler spell, and now the cures from the two Prison World, and also an Original along with the aforementioned items and the White Oak Stake along with a powerful enough witch.
  • So far he's the only character who has never had a past or present love interest.
  • Kai is a subspecies of witches called an aberrant witch that originally only had powers when siphoning magic from a source. Jo revealed that the Gemini Coven has had many of these aberrant witches in the past, and they were turned into vampires that had witch powers. Since they didn't have power before being turned, they are a loophole in nature that are vampires with the powers of witches, with their vampirism giving them an everlasting source to siphon magic from.
  • Kai is the last character to die in Season Six.
  • He is the first known witch in the series to be a vampire's blood source.
  • He returns in I'll Wed You in the Golden Summertime by stabbing his sister in the back during her wedding to Alaric.
  • Kai is the third main antagonist to have been killed in the season he debuted in.
  • Kai is the second main antagonist to have been killed permanently in a season finale. The first was Markos.
  • Kai is the fourth vampire (witch-vampire hybrid) to be bitten by Tyler.
    • Damon (Season Two), Caroline (Season Three), and Nadia (Season Five) were bitten by Tyler.
      • Unlike others, however, Kai survives by siphoning the magic out of the bite.
        • This also makes him the first vampire to be cured of a werewolf bite without needing Klaus' blood.
  • In I'm Thinking Of You All The While, Kai revealed that he used a Bennett's blood (de facto Qetsiyah's blood) to escape from the 1903 Prison World.
  • Kai is the second character to have killed a pregnant woman. The first was Damon.
    • However, both of them have failed to killed the children.
  • He and Jenna Sommers share the distinction of being the only vampires to be shown to be in transition, feed to complete their vampirism, and die all in the same episode.
  • He was a prisoner twice; once in 1994 and once in 1903 and both had been caused and/or helped by a Bennett witch.
    • Sheila Bennett gave the Gemini Coven her blood to create 1994 while Bonnie intentionally left him in 1903 as revenge for what he did to her.
  • Kai has never met Lorenzo.
  • Kai, like Stefan Salvatore, completed his transition to vampire by feeding on the blood of his dying father, Joshua Parker, like Stefan did to his father Giuseppe. Like Stefan, he is responsible for his father's death, Kai through his suicide, whereas Stefan killed his father by accident with his vampire strength causing his father to fatally stab himself.
  • Kai has Twitter account Cobrakai1972
  • Kai, along with Klaus, Katherine and Kol, are arguably the most popular villains in The Vampire Diaries. Ironically, all their names start with the letter "K". Fans have dubbed this group of villains Team K.


Kai (to Damon): "Rough day, huh, Damon? Sorry. Manners. I'm Kai. Nice to meet you. Pork rind?"
Kai (to Damon): "Oh, you think this is annoying? Hmm. Try listening to you and Bonnie bicker every 5 minutes."
Kai (to Damon): "Of course I have. You two are the closest thing I have a to a TV. I mean, you're no "Baywatch," but...Remember "Baywatch"? Oh. Oh, man, you got to watch it. You like lifeguards, like... Hot ones?"
Kai (to Damon): "Temper's gonna get you in trouble, Damon. It's already driven Bonnie away how many times? Oh, oh, oh, wait. I know. 13."
Kai (to Damon): "Ok. Ok. Sorry. Seriously. I'm just kind of rusty on the face-to-face type human interactions."
Kai (to Damon): "Maybe you should have a drink. That usually calms you down. Then makes you angry, then sad, then calm again. It's a weird cycle, and look, if you really want to know the reason I'm following you, it's because I want to kill you. Vervain in your bourbon. Who didn't see that one coming?"
Kai (to Damon): "Who buys patio furniture from a grocery store? I mean, somebody must. Otherwise, it... it wouldn't be here. But now I'm a little unfamiliar with vampires, but from what I've gathered, a stake in the heart should do it, right?"
Kai (to Damon): "You can always fight dirty, Damon. Like that time you and Bonnie played monopoly and you stole from the bank. Not cool."
Kai (to Bonnie): "The useless one is here. Thank God. I've watched you try to do magic for months now. What are you gonna do, fail at me? It's embarrassing. I'm embarrassed for you."
Kai (to Damon): "Let me guess. I answer right, I get a pork rind. Wrong, I get a poker."
Kai (to Bonnie and Damon): "The important thing is that you have your magic back. It worked. What, you... you didn't really think I'd kill Damon, did you? Heh heh. In what universe does that make sense? Who would kill 1/3 of our population? I'm not a monster. I knew Bonnie would show up. She always comes back, all 13 times, and I knew with the right motivation she'd be able to access her magic, although I-I did get a little worried with all your bickering that Damon's life wouldn't be enough motivation, but turns out it was. I guess that's just how you two show your love."
- Welcome to Paradise

Kai (to Bonnie and Damon): "And, of course, I broke into the Oval Office and took a picture of myself at the window, looking all JFK. But then, I was, like, "Wait-- How am I going to get these photos developed?"--"
Kai (to Bonnie and Damon): "Well, I heard you tell Bonnie this place was your own personal hell. I'm kinda curious why."
Kai (to Bonnie and Damon): "If you torture me, I'll get mad, and then I won't want to help you. What kind of person needs to have that explained to them?"
Kai (to Damon): "I was listening, in my sleep."
Kai (to Bonnie): "Ignore him, Bonnie. Pretend he's a white-noise machine. That's how I used to tune out my siblings. I grew up with a ton of little sisters and brothers. You know, all of them constantly yammering. But it taught me how to focus."
Kai (to Bonnie): "Yeah, but I wanted to feel your hand on my chest."
Kai (to Bonnie and Damon): "Who names a kid Malachai? It's like they expected me to be evil."
Kai (to Bonnie and Damon): "Hello! Not everyone died. I had a soft spot for one of my sisters. 'Cause otherwise, I would've cut her lungs out, and not just her spleen. You can survive without a spleen."
Kai (to Damon): "This place isn't your hell, Damon. It's mine."
Kai (to Bonnie): "Oh, come on, Bonnie. You wanna go home to your friends, I wanna go back and give the rest of the Gemini Coven an excruciating death. Win-win."
Kai (to Bonnie and Damon): "Here's the thing: I have a killer effect on magic. I can't generate it myself. But, I can consume it from others temporarily. My family called me an abomination. That hurt my feelings."
- Black Hole Sun

Kai (to Bonnie and Damon): "I heard my name. All good I hope."
Kai (to Bonnie and Damon): "Have you never portal-jumped through an eclipse before? Okay look, the light of the eclipse will shine down and activate the Ascendant, you spout a little witchy woo and then poof! Anyone standing in the circle of light holding the Ascendant goes home."
Kai (to Bonnie and Damon): "555-Hiya-Kai, no way I'm giving those digits up."
Kai (to Bonnie and Damon): "Look. The future sounds great, all right? I'm super excited about the Internet, but 1994 has been my home for most of my life. I'd hate to get homesick. So let's get down there--"
Kai (to Bonnie and Damon): "Forgetting someone?"
Kai (to Bonnie and Damon): "Did you really think I hadn't tried to kill myself before? Because I had-- lots of times, lots of ways."
Kai (to Bonnie and Damon about the Ascendant): "Grab that, and the next arrow goes in her heart. Your choice."
- The World Has Turned and Left Me Here

Kai (to Bonnie): "Right. Anyhoo, I have no idea how you managed to shatter the ascendant into a billion pieces, but we need to put it together before the eclipse at 12:28. You want to help? I know you're a puzzle person."
Kai (to Bonnie): "What was that? Huh? What? You're gonna do the spell and finally get us home?"
Kai (to Bonnie): "Looking for this? You stole the ascendant, naughty girl. You weren't planning on using and leaving me behind, were you? You left a trail of blood in the driveway. Figured where else would you stop and play nurse?"
Kai (to Bonnie): "I thought about taking the keys, but that'd be like taking the cheese out of a mousetrap, right, Bonnie? Although, you know, fun fact. Mice don't actually like cheese. Isn't that great? Shh, shh, shh. Shh, shh, shh. So we have an hour until the eclipse. It's time to go home, Bonnie."
Kai (to Bonnie): "I brought you a present. Ta-da! Ms. Cuddles! Thought you might want to bring her along."
Kai (to Bonnie): "I know you think I'm a monster. I mean, I did murder or heavily maim most of my immediate family, but after a long period of self-reflection, I've come to the conclusion that I could have handled my anger better."
Kai (to Bonnie): "I didn't mean it. Honestly, I would do anything to get my family back, and the thing I'm most scared of is trying to figure out how to live in the world again. Sort of hoping you've been a positive influence on me. You're a good person, Bonnie. You're brave, loyal, patient. I want to be more like you. (Kai uses a high-pitched voice for Ms. Cuddles) What do you say? Friends?"
Kai: "So long, 1994."
- Do You Remember the First Time?

Kai (to Jo): "Josette. Where are they? Oh, Jo. Come on out, Jo. I know you can hear me. Josette? Where are they, Jo? Hey. Everything's gonna be OK, all right? Everybody's just playing a game. You guys want to play a game? You want to play hide-and-seek? Shh. OK. Come on out, Jo. You know I won't kill you."
Kai (to Bonnie): "Wakey, wakey."
Kai (to Bonnie): "Get so lucky to arrive here on a private flight piloted by yours truly? Oh, you would have been super-impressed with my flying skills, but I'd already knocked you out with painkillers."
Kai (to Bonnie): "Portland, Oregon, stomping grounds of Courtney Love, Tonya Harding, and tons of other awesome people."
Kai (to Bonnie): "I've been counting eclipses since I was imprisoned on this empty planet, and according to my running tally, I've been here for 6,771 supernaturally repeating days, so in the real world, which we'll never get back to because you sent your magic away in a Teddy bear, today's my favorite day of the year. Thanksgiving. I'm cooking you dinner."
Kai (to Bonnie): "Ah. Memories. Pitter-patter of little siblings' feet, witchy-woo, chanting in the air, mom and dad calling me an abomination."
Kai (to Bonnie): "Because I can finally show it to someone. My coven goes out of their way to make sure no one finds us, but since they're not here to be paranoid freak shows, mi casa es su casa. Come on."
Kai (to Bonnie): "That smells great. Not exactly a turkey dinner, but it's what my family had in the fridge on May 10, 1994."
Kai (to Bonnie): "Don't tough that. Because it's brand-new, looks cool, and I don't want you to bust it."
Kai (to Bonnie): "I get it. I knocked you out, kidnapped you against your will. Can't you see I'm trying to apologize?"
Kai (to Bonnie): "Fine. Can we at least have one last dinner conversation before my eternity of aloneness resumes?"
Kai (to Bonnie): "In the spirit of Thanksgiving, I'll even let you take my car."
Kai (to Jo): "Where are they? (screams) Where are they?!"
Kai (to Bonnie): "Is it a crime to want to savor our last meal together?"
Kai (to Bonnie): "My family sent me to this prison world. My father, the great coven leader... he treated me like crap for 22 years and then locked me here. It's like his... like his kids didn't even matter. Coven always came first no matter what."
Kai: "Olivia, Lucas? Olivia? Lucas? Come out, come out, wherever you are."
Kai (to Jo): "Josette, what did you do? Why can't I feel your magic? And why aren't they saying anything? They should be saying something. They should be saying something, right? We're merging. This should all be a bigger deal."
- Fade Into You

Kai (to the taxi driver): "You ever worn skinny jeans? Agh. It seems wrong. I'm all bunched up. Also, why are jeans so tight when phones are so big?"
Kai (to the taxi driver): "Oh, God. I'm that guy, right? That guy that won't shut up. Oh, I hate that guy. I just sat next to that guy on the plane. He was the worst. Hey. Speaking of planes, have you flown recently? Because what's with the whole liquid situation and the stripping before you go through security thing? It's weird."
Kai (to the taxi driver): "Ok. Well, I'm sorry, but the real terrorists are some of those people taking off their shoes. I know I'm chatty. Sorry. I've just been in prison for awhile. Not like a regular prison, you know, more like a..."
Kai (to the taxi driver): "All right. Jeans. Uh, will you take this? Hang on. Hang on. I got it. Oh. Hey. Gum. Nice."
Kai: "Heh. ‘’Liv’’. Ironic."
Kai (to Liv): "You on Twitter? Ah. I just signed up. You should follow me. Cobrakai1972. Come on. Like "Karate Kid"? Did you know you can follow celebrities? Heh. They all Twitter the stupidest things. It's-it's hilarious."
Kai (to Liv): "Oh. Hang on, hang on. I'm gonna get a real drink. No bourbon. I'm secure enough in my masculinity. Vodka's boring, rum's too tropical. Ooh. Tequila. You do not want to see me on Tequila. What about gin? Is that weird?"
Kai (to Liv): "No. True story, but that's not the most interesting thing on that I.D. Here. Look again. Name, address..."
Kai (to Liv): "Last time I saw you... I was trying to kill you. Why don't we pick up where we left off?"
Kai: "Life is so much easier with magic."
Kai (to Liv): "Feels kind of like cheating. I'm sad you didn't recognize me. That means dad erased all trace of my existence-- family pictures, movies, little handprint turkey I made. What a dick."
Kai (to Liv): "You were always so bad at hide-and-seek. I mean, you were 4, but still, find a better hiding spot."
Kai (to Elena and Damon): "Wait. Are you guys talking about Bonnie Bennett? Because honestly, I didn't think she was all that great."
Kai (to Damon): "Oh, hey. Me, too. Oh, yeah. Damon, I, uh, I stole some of Liv's magic when I tried to kill her. Think some of it might still be in my system, so pardon me."
Kai (to Elena and Damon): "Huh. I guess this is that, uh, anti-magic border, which means now there's a psycho loose in Mystic Falls and no vampires around to stop him. Whoops."
Kai (to Tyler): "I think gin gets a bad rap."
Kai (to Tyler): "I'd rather not kill you, but I will."
Kai (to Tyler): "This is gonna sound crazy, but I want to save Liv's life. Feel like making a deal with the devil?"
- I Alone

Kai (to Jo): "I stabbed her."
Kai (to Liv and Luke): "I know I tried to kill you when you were toddlers, but I got to say, it sure is nice to be around family for the holidays."
Kai (to Liv and Luke): "Sissy's up."
Kai (to Jo): "I haven't seen you in 18 years. You can't muster a hello?"
Kai (to Luke): "I'm trying to reunite Jo with her... (He stabs her again) magic. It's not working."
Kai (to Luke): "I was wanting to kill you when your brain was the size of an acorn. You don't think I'll do it now?"
Kai (to Jo): "Oh, so dramatic. All right. Sissy... Let's try this again."
Kai (to Liv): "I'm going to find a bandage while you figure out how to put the magic in this knife into our sister. Preferably by the time I get back so I don't have to dull it by slitting your throat."
Kai (to Jo): "Isn't it gonna be funny when I kill her using her own magic? Wait. Is that funny or sad? I get my emotions mixed up. Hey. What's the one for fire again? It's "incendia," right? Phesmatos..."
Kai (to Damon): "Oh, whoops. Looks like you found the anti-magic border. Drew a line in the dirt for everyone's convenience. See? Yeah. You're welcome."
Kai (to Damon): "So this whole anti-magic thing, is it like a... Like a dome or a bubble? Like, say, you were in 747 flying over Mystic Falls, would you die? You know, that could be dangerous, like if you're headed to New York and your pilot reroutes for weather."
Kai: "That's a lot of travelers. Must be a pretty big spell. Like a really big spell. So big... it covers every inch of an entire town."
Kai (to Elena): "I may have put a cloaking spell on us. How genius is that?"
- Christmas Through Your Eyes

Kai (to Elena): "See, we never went out to dinner when I was a kid, so, I always had this fascination with chefs and fine dining. Dad actually let me cook... Taught me to measure by eye. Seasonings to taste, all that stuff, but it's different now in the restaurant world. Everything's on time. It's like, the fries go in, you push a button, it dings and you take 'em out. Literally no guess work."
Kai (to Elena): "Uh, well I spent eighteen years in abandoned restaurants and now I'm showing off the fruits of my labor."
Kai (to Elena): "Oh, you mean like, here here, in Mystic Falls. (laughs) Sorry, I'm nervous. You're like, really pretty."
Kai (to Elena): "Well I took this spell that was keeping supernaturals out of Mystic Falls and I like absorbed it. Like ate it I guess. It’s cool, huh? First, I eat magic and then eventually I lose it. But, with a huge spell like that. I mean, come on, magic’s oozing out of me. It’s all over the place. You know, I didn’t quite realize, I was so out of control until I met the manager of the grill a few hours ago and he was all like, “Yeah, you can’t come in here, we’re closed, and you have an unconscious girl over your shoulder.” And I was like, “Don’t judge me.” So, then I gave him a heart attack. Tried to. But all I did was make him vomit uncontrollably, which was like, uh, all right, let’s stop that. So, I tried again, and I think I broke his spine. I’m not- I’m not really sure, because the third time I tried the spell, he kind of exploded in blood. Whoops."
Kai (to Elena): "I just told you, I have too much magic. You know, it wasn't until after my test run with the manager that I realized, if I start to merge with Jo and my gushing fountains of magic turn her into that guy, then I'm not gonna have a twin for the merge. So, Elena, that is why you are here. Because I need to get my magic under control. By practicing with you. Or rather, by practicing on you. Oh, PS: Silver lining, after the manager finally stopped thrashing around, I finally managed a cloaking spell. Thank you. It's easy to do and...undo. Phasmatos oculix. (Dead manager appears on table in front of Elena) Table for three. You had no idea."
Kai (to Elena): "They have plenty of restrooms, no flammable surfaces, and everyone's on winter break...Still. You know, it's no wonder America got dumb while I was locked up; they're never in school. (Looking at pictures in the trophy case of the cheerleading squad; grinning) Is that you? Oh, and there's Bonnie. You guys look so innocent. Smiling, like nothing bad could ever happen to you. Anyway, do you mind if I try to turn your blood into acid again?"
Kai (to Elena): "Take it that ring meant something to you? I never understood sentimental attachments to things, because then it's so upsetting when you lose them."
Kai: "Really? Dammit. Bingo."
Kai (to Elena): "Well, thanks. Yeah, somebody burned my other one. Which was awesome, by the way."
Kai (to Elena): "I am starting to see why Damon digs you. You are crazy-pants. Oh, it sucks about that shirt, though."
Kai (to Elena): "Oh. Is this going to be like an episode of "Ricki Lake" where I come face-to-face with my demons and change for the better?"
Kai (to Elena): "I guess I liked my brother, Joey. We played Dr. Mario together and he'd always win. Actually, one of my favorite memories is when I finally beat him. Of course, my favorite memory is when I finally beat him to death. You don't have to waste your energy trying to change me. If Ricki taught me anything, it's that liking yourself is the most important thing. And I like me."
- Woke Up With a Monster

Kai (to Damon): "You really think I'm gonna trust you?"
Kai (to first Tyler then Damon): "Hi. Let’s discuss my fee."
Kai (to Elena and Damon): "I get what you two see in each other. It’s very dys-fun-ctional. Ha! You see what I did, stressing the “fun” in dysfunctional."
Kai (to Jo): "Hey sis, little busy. Be with you in a jiffy."
Kai (to Elena): "Oh, that is so tragic. You know, 'cause you guys jumped through hoops to get the magic out of her system, but then her ticker's just not strong enough to take a little siphoning."
Kai (to Jo): "Magical neck snap. Never gets old. Isn’t this the part where you start running?"
Kai (to Jo): "Look at those pretty planets, all twinkly and bright. Oh, Josette, you would not believe how sick I am of eclipses."
Kai (to Luke): "Fine. It’s your funeral."
Kai (to Jo): "You know, if you think I didn't spend the last 18 years in solitary thinking about you screwed me over last time, you're wrong. So if this is just another setup, I'll rip something out more important than a spleen. Like a tongue or a heart. So, any closing remarks?"
Kai: "You win some, you lose some. Except for me. I always win."
- Prayer For the Dying

Kai: "Oh! Forgot how massive this house was. Yum! Cupcakes!"
Kai (to Elena and Damon): "Funniest thing. I need your help."
Kai (to Elena and Damon): "I haven’t been able to find her using the locator spell, and, you know, good on her because under normal circumstances, I’d be superjazzed to gouge out her belly button."
Kai (to Elena and Damon): "Well, in case you haven’t figured it out by now, I’m a sociopath. I know. Shocker. I like being a sociopath. You know, I’m not burdened by things like guilt or love. So then this merge happen with my brother Luke. And I won, which is just great because I absorbed his ability to do magic. But now, I can’t stop thinking about how Luke died. How Liv’s life is ruined. For some horrible reasons, I can’t shake. I feel bad. So when I absorbed Luke’s magic, I must have gotten some of his qualities or something. Like empathy. So, I googled how to process emotional pain. And they said if you write everything down in a letter and burn it, you’ll heal. So I started writing, and this water literally started pooling in my eyes. As that ever happened to you? Like- like water just- just oozing out of my eyeballs like I’m some alien creature excreting fluids."
Kai (to Jeremy): "Think of it like, Elena in reverse. You know she was human, pure, dating the good Salvatore. Then she became an undead blood-vacuum, stopped caring about right and wrong, started dating the bad one... I'm sure I missed a detail or two, but I'm just paraphrasing what Damon told me in the Prison World."
Kai (to Elena and Damon): "Oh, thank God. You two together still totally revolting to me. Finally, a familiar feeling. Luke didn’t take me over completely."
Kai: "You see this blood? I’m guessing that’s not a good sign."
Kai: "All while sending the three of you back over there? Sure. Yeah. Hey, why don’t I reanimate your dead parents for a tea party while I’m at it?"
Kai (to Liv): "Dang, sis. That was harsh."
Kai (to Liv): "It’s all coming back to me, Livvie Poo. You know the charge… that race through your bones… at the prospect of watching someone burn to death? I really missed that feeling."
- The Day I Tried To Live

Kai (to Jo): "Look. There’s an issue that I’ve been worried about since the merge because we didn’t really do it right, you know, the whole… “You’re not my twin” “Hey, that’s ok, close enough” plan? It worked which is, you know, cool. Hey. I’m even a little bit nice now. In case you were wondering. But I’ve been waiting for the issue to drop. And well I think it dropped. Because I’m- Where’s the bathroom?"
Kai (to Jo): "I don’t think you have food poisoning. I was supposed to merge my magic with you. But I got Luke’s instead. Oh. And now I’m defective. And that’s why I think you’re sick. Kind of feel like I’m dying actually. If I die, so do you, dad, Liv and the rest of our dumb coven. So, would you please fix me? Like, now?"
Kai (to Jo): "This is kind of private. Does your baby-boo need to be here?"
Kai (to Jo): "Yeah, duh. Because I’m magically diseased."
Kai (to Alaric): "You need to give me your magic. This faux merge is clearly falling because I was supposed to get your magic, right? Just- I don’t know- Put it in a- Put it in a Teddy bear or a bed pan or whatever and gimmie!"
Kai (to Alaric): "I can see you’re skeptical, Ric. Can I call you Ric?"
Kai (to Alaric): "If I die, the worlds collapse, all right? I see vacancy. Would you like me to start over with single syllables?"
Kai (to Jo): "Me, our coven, and the prison worlds thank you."
Kai (to Alaric): "A place filled with crappy people like me, I’m sure."
Kai (to Jo): "Oh. Don’t look so stressed."
Kai (to Jo): "Thank you. And congratulations. Have a good life, sissy."
- Let Her Go

Kai (to Damon): "I can’t believe Bonnie made it out. Actually I can. She’s plucky."
Kai (to Damon): "Hey, do you need help? Oh. Before you answer that, I’d rather not. Just keep experiencing these pangs of guilt watching you. Feelings are hard."
Kai (to Damon): "Damon, Bonnie saw her alive in a 1903 prison world. It’s on camera. You want to watch it again?"
Kai (to Damon): "I’m just saying. Digging up mommy’s grave? That’s dark, even for me."
Kai (to Damon): "Mom’s in a prison world and therefore an evil psychopath. Don’t want to ruin little bro’s perfect mommy memory."
Kai (to Damon): "Well, ever since you told me Bonnie was back, I, uh-, I can’t stop thinking about her."
Kai (to Damon): "I need to see her. I need to apologize. And you’re gonna make that happen."
Kai (to Damon): "But there is a new me. You… you explained it to her so she would understand, right? Small words, easy to digest."
- The Downward Spiral

Kai (to Bonnie): "You want the 1903 ascendant. Well, sure. Just let me reach in my pocket and pull it out. Wait. Oh, that’s weird. It was in my pocket."
Kai (to Bonnie): "I’ll go if you go. Come on. It could be fun. You know, 1903, the gilded age. Didn’t you ever dream about time travel?"
Kai (to Bonnie): "Damn. Crocodile Dundee called. He wants his knife back."
Kai (to Bonnie): "You have really nice palms."
Kai (to Bonnie): "Please! Believe me, I've changed."
- A Bird in a Gilded Cage

Kai: "It’s time we get the hell out of this place."
- I'd Leave My Happy Home For You

Kai (to Bonnie): "Woah. You are not good at running."
Kai (to Bonnie): "No magic? Oh that's my fault. I was spooning you earlier. I think I might’ve sleep siphoned you. How you keep trying is just adorable like you're a having a seizure."
Kai (to Bonnie): "Did you think you could keep screwing people over and there wouldn't be any consequences?"
Kai: "I was gonna wait till the "death do us part" bit. But it seemed a little on the nose. Am I right?"
Kai: "Miss me? No? Oh, well."
- I'll Wed You in the Golden Summertime

Kai (to Stefan and Caroline): "Nothing personal, but this is a family matter now."
Kai: "Let me guess. Prison world? Ooh. But you can't kill me cause you all die too, right?"
Kai (to Alaric): "Hey, I'm sorry about your twinsies. I just don't feel like competing for leadership against future Gemini twins. See, when your family decides that you're nothing but an irredeemable piece of trash, well, guess the best thing to do is prove them right, right?"
Kai (to Joshua): "Here's to being different, dad."
Kai (to Alaric): "Bad time?"
Kai (to Alaric): "Freaky, right? I turned myself into one of Lily's Heretics. It's really incredible actually. I can literally siphon the magic of my vampirism and convert it into more magic
Kai (to Alaric): "Ouh. Looks like somebody's having a really bad day."
Kai: "Bad doggy."
Kai (to Bonnie through a camera): "All this time travel's has been hard on the camera, Bon. Yay! You saw the post-it. This message will self-destruct in ten seconds. Kidding. Anyhow, you're probably wondering why you're still alive, since I should have bled you out, one painful ounce at a time. I mean, that's what you deserved. You left me behind in 1903, which I did not appreciate, but I guess you forgot about that old Canadian rock filled with Bennett blood. Anyway, even though I got out, I kind of just want to make you suffer, in new and-- if I may say so myself-- totally inspired ways."
Kai(to Damon): "What's happening to me?"
Kai(to Damon): "It's just not as threatening when I'm seeing like, four super-blurry versions of you."
Kai: "Young, beautiful, human Elena Gilbert, preserved in this moment indefinitely."
Kai (to Bonnie through a camera): "So, Bonster, I linked Elena's life to yours. The rule is-- as long as you're alive, Elena will remain asleep."
Kai (to Bonnie through a camera): "And oh, please don't go looking for some weird witchy work-around, because as the incredibly-powerful leader of the Gemini's, I rigged this so that if you do try to outsmart it, both you and Elena will die-- instantly. I guess what I'm trying to say is your betrayal really hurt me, Bon. So, this is kind of all your fault."
Kai(to Damon): "Damon, think about it-- everyday that you wake up without Elena in your arms, you'll have the burning desire to kill Bonnie. Of course, you could just get it over with and kill her now, but Elena will probably never speak to you again."
Kai: "Hello! Anyone still alive, hm? Anyone alive, just raise your hand. I need blood."
Kai (to Bonnie): "Do your friends think you're funny? Because maybe if you were funny, if you were the one with the good jokes who they could always count on to make them laugh, maybe they'd be cool with letting you live instead of Elena."
Kai (to Bonnie): "I can't, what's done is done."
Kai (to Bonnie): "I can't undo the spell, Bonnie. My death made it permanent."
Kai (to Bonnie): "You know what's funny? I didn't even know werewolves were real until I got bit by one. The thing is, Bon-- the only way a guy turns into a wolf is if it's magic, right? So technically, their venom's magic, too. So I just went ahead and siphoned it up."
Kai(to Damon): "How dumb are you? I deliver you a dying Bonnie Bennett on a silver platter and woosh, right over your head."
Kai(to Damon): "Uh, translation: she's about to croak. Of course, you don't have to help her, you could just walk away. She dies of collapsed lung, no blood on your hands, and you and Elena get to live the life you always dreamed of. Either way, you better act quick."
Kai (to Bonnie): "That’s it? He just left you? The whole point was that this will torture him for awhile. I mean, you'd think he'd at least flip a coin. Heads he picks you, tails he picks -"
- I'm Thinking Of You All The While



See also